My friend with benefits, Penny, and I had been having a complicated on-again-off-again relationship for about three years at this point. I loved her like a friend, the sex was usually incredible, and she was fun to spend time with. However, I didn’t see myself ever wanting to marry her or have kids with her or anything of the sort. I was hitting a point in my life where I was starting to think that it might be the right thing to try to ‘settle down’ and find someone I actually wanted to be with.
I changed my OkCupid profile to one that was looking for something a little more serious and started to message women that I might be interested in. Worth mentioning, Penny and I were also on AdultFriendFinder with a couples profile — though that had stalled out significantly — and I had my own solo profile for trying to find women for something casual.
One day on OkCupid I matched with a gorgeous brunette. She lived in the next major city away from me — about 45 minutes to an hour drive — had flawless pale skin, hazel eyes, and a look of confidence about her that was very appealing. Her photos all appeared to be professionally done and I came to find out that she was an aspiring opera singer. Our banter was really strong, she was incredibly smart and well educated, and she was very classy in her approach. I had gotten used to the… well… kinda slutty way in which Penny behaved and it was a nice treat to meet someone that was Penny’s polar opposite.
We decided to meet for lunch for a first date at some French bistro near her. I wanted to impress her so I got dressed up a bit. Oddly, and very much in the vein of who I am, I was also incredibly horny and was ‘saving up’ in case we ended up hooking up that day. I knew — or at least hoped — it would be a long shot since I wanted her to be a different kind of woman than I was used to, but I was getting worked up thinking about it. That led me to AFF and messaging a few women that morning while I waited for the lunch hour to arrive.
Interestingly a woman I had messaged a few times before on AFF responded that day and she invited me to come over to her house for a hook up. The overly horny and insatiable part of being a 26 year old man kicked in and I agreed; hoping that I would be able to bust a nut and then meet this opera singer for a nice date. I jumped at the opportunity and agreed to meet this AFF woman in 15 minutes at her apartment; she lived very close to me and that made it all the more enticing.
I showed up at her apartment, she let me in, and I wasn’t feeling it, but I was going to do it anyway. I recall that she was a blonde, thick hips, small breasts, and — while she wasn’t ugly — she wasn’t very pretty either; 5/10, max. I was feeling overly confident in myself. I was in the best shape of my life, dressed-up for a date, having regular sex with much more attractive women than the one I was about to. That all came tumbling down a moment later.
I was eager to get started since I had a date in about an hour and a half, “So what do you want to do?” I asked playfully.
“So, this isn’t cool.” She said after an intense pause. “You don’t look anything like your pictures.”
I was puzzled, “What? What do you mean.”
“You,” she gestured at me, “you don’t look like your pics. I feel like you lied to me.”
“I have never had anyone tell me that before.” I responded genuinely. I was very good at keeping all of my photos current and sending both goofy photos and good ones to make sure there was no chance of someone not being aware of what they were getting into.
“Yeah, this isn’t okay and I am uncomfortable.”
“Oh my god, what? I’m… I don’t know what to say.”
“Yeah those photos aren’t you.” She was dead serious and looked angry.
“Well, they are. I’ll go though.”
“Yeah you better go. You aren’t in those pictures.”
I was flabbergasted and really embarrassed. I grabbed my jacket, walked out of the apartment, and got in my car. I was nervous sweating and couldn’t stop running the conversation through my mind. That girl had been dead serious that I wasn’t the guy in the photos and I was starting to wonder what that meant. Was I not attractive anymore? Had I lost my mojo? I sat in the parking lot for a minute before heading to my date and ran that awkward situation over in my mind 100 times.
When I arrived at the bistro my date, we’ll call her Bethany, was already there. She smiled warmly when she saw me and looked incredibly regal. We sat down and I was a little flustered trying to summon my normally charming nature for a decent conversation. At one point I decided I would just sacrifice the date and ask about my photos — many of the photos on my OkCupid were the ones I had sent to the AFF woman earlier that day.
“Do I look like my photos?”
“100%” Bethany smiled, “You are really handsome.”
“Really, nothing unexpected?”
“You’re taller than I thought you’d be.”
“Really? I said I was 6’2” on my profile.”
“Yeah, but most guys lie. I expected you to be a little shorter.”
“No, no reason to lie. I am who I am.”
I started to get my mojo back and the rest of the date was amazing. We walked around the city a bit, flirted a lot, and I left without a kiss but with a second date all but scheduled. I ended up going to see one of her performances the next weekend and dropping off some flowers for her as a gesture. The next weekend we went out again for dinner and we were really hitting it off. At the end of the night she asked me if I wanted to come over to her place and stay the night.
“I would love to.”
She lived in an incredibly nice part of town in a huge house with — I was told — two other roommates, both of whom I never met despite that we dated for about four months. Bethany gave me a tour of her house ending at her bedroom.
We kissed for the first time and it was nice. I had gotten used to the kind of kissing that you do when you are trying to turn your partner on so that you can fuck like wild dogs. This was the kind of kissing you do when you want someone to fall in love with you. Slow, deliberate, passionate. It was a welcome change of pace and this was the right woman to do it. I pulled her in tight so that I could feel her body against mine. She had the look of a a curvy woman — like Kelly Brook in her heyday — but when I felt her body against mine I realized that there was no fat on her at all. I later found out that she did yoga 5 – 7 days a week and needed to be in peak shape to keep her voice healthy and powerful.
We made out for what felt like ages. I slowly began to explore her body with my hands, grabbed onto her muscular ass, her enormous breasts, and her shapely hips. I made sure to keep her pulled in close to me so that she could feel the size of my ever-growing erection against her legs or stomach. Eventually, I guided her hand down to my crotch so she could stroke my manhood and get a better feeling of it while I kissed her neck.
Things escalated very slowly that night making things all that much better. Each article of clothing that came off took several minutes as we continued to tease and entice one another. When I finally saw her nude I was amazed. Her body was indescribably perfect in so much as it matched her personality, her beauty, and her charm.
We continued to make out, nude, laying in her bed, our hands exploring each other in every way. She had a gorgeous pussy with a well trimmed patch of pubic hair resting on her pubic mound. Her lips were as pale as the rest of her skin and begging for me to kiss them. I slowly kissed my way down her body. I spent an eternity sucking on her nipples and playing with her breasts. I had only been with one person before her that had been so well equipped with such flawless natural D-cups.
I licked and kissed along her abdomen and gave each of the muscles there a welcome greeting. When I got to her thighs I parted them and stared longingly at her womanhood. I took my time carefully making my way down each leg kiss by kiss until I reached her pussy. I would kiss her clitoral hood, then start back at the knee of the next leg and work my way back down. She would moan these perfect soprano tones each time this tease of my mouth pushed her further along.
When I felt like she was ready based on the way she looked down at me as I hovered over her pussy I made my move. I licked the entirety of her soft wet slit slowly; making sure she could see the tip of my tongue the entire time. She cried out in satisfaction as I reached her clit and she melted into the bed. I went down on her for a very long time. We had probably been at it for two hours before I finally licked her and it was probably another hour of licking before she told me she wanted to take me into her mouth.
She got on her knees at the side of the bed and had me sit there looking down at her. The angle was amazing, because it forced my cock to be pulled down far to become parallel with the floor. That sensation was incredibly intense and the sight of her talented mouth and beautiful face looking up at me was pushing me over the edge. She wasn’t the most talented, but she was the most dedicated person I had ever had suck my cock. She was trying to slowly tease the cum out of me like I had done for her, but all it was doing was making me want to fuck her more and more. I told her as much and she seemed to hesitate. I thought that perhaps she was going to want to wait for another night, but she was just worried about how big I was.
“I’ve never seen a penis as big as yours.” She admitted sheepishly, “I don’t know if I can take it.”
I was overjoyed. I loved to hear a woman talk about my cock like that. I knew that I wasn’t huge — but being bigger than the last guy — or all a woman’s ‘last guys’ was a major turn on for me. I told her that we could stop for now if she wanted, or that I could simply go very slowly.
“I want to feel you inside me.” She told me. “Just go slowly. Please?” It was more question than a request.
She gave me a condom from her nightstand and I told her it was a little small and it might break. I rolled it on as I slipped two fingers insider her to make sure she was wet and ready. She gasped and moaned and writhed her hips in motion with my fingers. Even her pussy was muscular and I could feel her squeezing down on my fingers when I did something she liked. I spit on my condom covered erection and then spread her wetness and my saliva all over my cock. When I felt sufficiently wet I aligned myself with her and slowly began to enter.
She was right, she was tight, and this was a process best approached slowly. I ran my hands over her body and purred for her to relax for me as I slowly entered her. I felt like I took a minute per inch to push inside her and she gasped and whimpered a few times along the way. When I was finally fully insider her, my pubic bone pressed into hers, I kissed her hard and deep and we just enjoyed the moment of it. I wasn’t rushing to cum, I was savoring it.
When she was ready I began to thrust in and out of her slowly. Watching her body react to how I made her feel. We made love for a long time that night or at least it felt that way. It was so slow and beautiful that it seemed to last for an eternity. This was very different than I had, had the past few years and it was exactly what I needed; exactly what I didn’t know I wanted, but finally had. She came for me several times and they were fantastic. She wasn’t thrashing and screaming, she would become calm and breathy and tighten up everywhere. Each time she came she would kiss me deeply and hold me to her tight.
When my time finally came I pulled out and discarded the condom so I could empty myself onto her flat little tummy and big full breasts. She watched the whole time and cooed her pleasure as I pumped and pumped and unleashed the thickest strings of cum I had.
I saw her twice a week for the next few months and we had the most peaceful, patient, loving, and kind relationship I had ever had to that point. I had all but cut off my FWB, Penny, except from texting occasionally, as I was too busy and too interested in Bethany. Obviously, I ended things with Bethany eventually. There was a lot going on in my head at the time. I was torn between the sweet and loving thing I had with Bethany; the incredible friendship and sex I had with Penny; and a woman from my past that I was still pining for and who was never far from my thoughts, Rebekah. I started to realize that if things went further with Bethany I would need to nix Penny and I would never have the chance to be with Rebekah again as I was not going to cheat on Bethany.
The last time I saw Bethany we had dinner somewhere nice and had a conversation that somehow led to marriage. She expressed her interest in doing that one day and how she envisioned it and I realized I was about to hit the point of no return. I knew she wasn’t ‘the one’ so when we got back to her house that night I asked if we could just be friends. I think about Bethany sometimes and wonder how she is doing. She was an incredible person and she deserves all the best things in life.
Source: reddit.com/r/gonewildstories/comments/n2ingl/the_opera_singer_mf